Cynthia Taylor, senior vice president of agent software and advertising at Zillow, is reshaping how technology supports real estate agents in a rapidly evolving market. She oversees a broad portfolio of tools designed to help agents grow their business and deliver standout client experiences. This year Taylor landed a coveted spot on RISMedia’s 2026 Real Estate Newsmakers list in the Trailblazers category for her 2025 efforts leading agent-focused innovation and unveiling a suite of new tools designed to elevate service from first showing through final offer.
Here, Taylor speaks with RISMedia, diving deeper into her role overseeing a broad portfolio of Zillow’s agent tools, what agents need most for technology, how seismic industry shifts have shaped Zillow’s product priorities and balancing automation with the personal relationships that are invaluable to agents’ success.
RISMedia: You oversee a remarkably broad portfolio—from Follow Up Boss to ShowingTime to Zillow Showcase. How do you think about making those tools work as a cohesive ecosystem rather than just a collection of separate products?
Cynthia Taylor: The portfolio looks broad from the outside, but from where I sit, every one of those products is solving a version of the same problem: How do we help agents show up for their clients at exactly the right moment, with exactly the right information?
Each product touches a different part of that journey. But where things get really interesting is when they work together—a showing request that flows into a follow-up task without the agent having to think about it, financing signals that surface automatically in the CRM, a contract that doesn’t require starting from scratch in a separate system.
A Zillow Pro membership is where this becomes most tangible. It’s the first time an agent can take Zillow’s consumer intelligence and their Follow Up Boss workflows and treat them as one system.
On the listing side, we’ve also made real progress in how Zillow Preview, Zillow Showcase, and Zillow Pro can connect when an agent wants them to. There’s now a natural progression: build early demand through Preview, present the home at its best through Showcase, stay connected to the right buyers through Pro. When agents experience it, they feel like things are finally clicking the way they should.
That’s really the goal. To meaningfully solve problems for agents, we need a system where the whole is greater than the sum of its parts.
RISMedia: After over a decade at Zillow, how has your sense of what agents actually need from technology evolved?
CT: I used to think agents needed better information. And while that’s true, it’s only part of the equation. What agents actually need is to free up mental energy—energy they’re losing to things that have nothing to do with why they got into real estate, like double-entering data, chasing transaction statuses, and manually following up on leads that went cold. The job they want to do is guide people through one of the most stressful decisions of their lives, but the job technology forces them to do is administrative work.
Spending time with agents from all over the country over the course of a decade changes how you see the job. The emotional weight they carry for their clients is real. When a deal falls apart two days before closing, that’s a person’s real life being disrupted. The best thing technology can do is make sure agents are not also absorbing unnecessary operational burden on top of providing the human element that makes agents so integral.
My Agent—through a Zillow Pro membership—is a clear expression of how we’re working to solve for this. When a contact agrees to collaborate with an agent through Zillow Pro, an agent can see when someone in their sphere is actively searching on Zillow, so the outreach is timed to the moment the client is already in the right mindset to engage.
RISMedia: The real estate market has gone through enormous turbulence—rate shocks, commission structure changes, inventory crunches. How has that volatility shaped your product priorities?
CT: If anything, it clarified our thinking. Our job isn’t to build for a hot market or a slow one—it’s to build tools that make an agent successful no matter what the macro is doing. That’s the standard we hold ourselves to.
What that looks like in practice: Helping agents win with buyers and sellers who are ready to move today, and staying meaningfully connected to the people in their sphere who aren’t ready yet. Both matter. A down market doesn’t mean there are no clients—it means the agents who stay present and trusted are the ones who earn the business when the moment comes.
That’s a through-line across what we build. Whether it’s connecting agents to new clients or giving them the tools to nurture their sphere through a Zillow Pro membership, the question we keep asking is: Does this work in any market? If the answer is no, we have to rethink it.
RISMedia: What’s a product decision you’ve made in the last year that you’re most proud of, and one you’d do differently?
CT: The one I’m most proud of is how much we’ve expanded what we can offer sellers—and by extension, the agents who represent them.
Showcase raised the bar on what a listing presentation can actually be—not just better photos, but a more immersive experience that changes how buyers emotionally engage with a home. The data backs it up on views, saves, and price outcomes. Preview extended that further by giving sellers meaningful exposure before they even go active, so real demand is building before the first showing. And a Zillow Pro membership connects the agent’s sphere to all of it, so the right buyers are paying attention throughout.
What I’m proud of isn’t any one of those individually—it’s the conviction that sellers deserve a better experience, and that we kept investing in that even when the adoption curve felt slow and the questions were hard.
One area I’d reflect on is the balance between buyer-side and seller-side investment. For years, Zillow was laser-focused on building tools for homebuyers, and we built some of the best in the industry. In hindsight, we could have turned our attention to the seller experience sooner. That said, I don’t see it as a misstep so much as a natural sequencing. Our deep understanding of buyers—what they need, how they search, what drives their decisions—gave us a uniquely informed foundation for building seller tools that actually close the loop. The investment we’ve made in the seller experience over the past few years is stronger because of that buyer-side groundwork. So while I might have accelerated the timeline, the journey was important.
RISMedia: You’ve said technology should elevate the human touch rather than replace it. But there’s real tension there—at what point does automation start to erode the personal relationship that makes a great agent great?
It’s a real tension but, for me, the line is intent. Automation that handles the logistics of a relationship—the scheduling, the reminders, the follow-up cadence—frees up an agent’s attention for the moments that truly require their human expertise.
Likely to List—another premium feature available with a Zillow Pro membership—is a good example. It uses AI to flag contacts in your database whose property indicates they may be getting close to selling, so the agent has a real reason to pick up the phone. The technology identifies the opportunity but the agent owns the relationship and the conversation.
The agents who are really making technology like this work for them use it to make sure nothing falls through the cracks, and then they show up fully in the moments that matter. Buying or selling a home remains the most important transaction in most people’s lives. Done right, AI, and technology can help make great agents more productive while simultaneously elevating the experience and service they provide to their clients.
For more information, visit Zillow Showcase.
